(5R,9R)-5-((3,5-dimethylphenyl)amino)-11-ethylidene-7-methyl-5,6,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-2(1H)-one

ID: ALA4865358

PubChem CID: 164620895

Max Phase: Preclinical

Molecular Formula: C23H26N2O

Molecular Weight: 346.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C/C=C1\[C@H]2C=C(C)C[C@]1(Nc1cc(C)cc(C)c1)c1ccc(=O)[nH]c1C2

Standard InChI:  InChI=1S/C23H26N2O/c1-5-19-17-9-16(4)13-23(19,20-6-7-22(26)24-21(20)12-17)25-18-10-14(2)8-15(3)11-18/h5-11,17,25H,12-13H2,1-4H3,(H,24,26)/b19-5+/t17-,23+/m0/s1

Standard InChI Key:  YVQINAZYWLASBT-LJUPNIGYSA-N

Molfile:  

 
     RDKit          2D

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   11.0597   -3.1611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9731   -3.1528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1023   -2.3563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5092   -3.6031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6343   -2.7983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8488   -2.0559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6028   -3.6615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5843   -1.8140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5977   -2.7817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4785   -2.5690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9888   -2.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4016   -1.6264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3534   -3.3696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4684   -3.8825    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0922   -4.3246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2584   -2.2686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8104   -0.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2581   -4.3246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8003   -2.7941    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1815   -4.2954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1778   -5.1205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8900   -5.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6051   -5.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6035   -4.2938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8906   -3.8848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8887   -6.3590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3177   -3.8793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  1  1  0
  5  4  1  0
  6  3  1  0
  7  2  1  0
  8 12  2  0
  9  5  1  0
 10 13  1  0
 11  1  1  0
 12 11  1  0
 13  7  2  0
  1 14  1  1
 15  4  2  0
 16 10  2  0
 17 12  1  0
 18 15  1  0
  5 19  1  6
  5  8  1  0
  3  9  1  0
  6 10  1  0
 14 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 22 26  1  0
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4865358

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 346.47

Molecular Weight (Monoisotopic): 346.2045

AlogP: 4.77

#Rotatable Bonds: 2

Polar Surface Area: 44.89

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.06

CX Basic pKa: 3.89

CX LogP: 3.72

CX LogD: 3.72

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.77

Np Likeness Score: 0.85

References

1. Miao SX, Wan LX, He ZX, Zhou XL, Li X, Gao F..  (2021)  Pd-Catalyzed Direct Diversification of Natural Anti-Alzheimer's Disease Drug: Synthesis and Biological Evaluation of N-Aryl Huperzine A Analogues.,  84  (8.0): [PMID:34445873] [10.1021/acs.jnatprod.1c00600]

Source

Source(1):

• Scientific Literature